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From $275 per night (USD)
VRBO
Tropical Tee Time Villa
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to a stunning vacation rental in Key West, nestled on a picturesque golf course within an amazing resort. This pr ...
From $275 per night (USD)
VRBO
$Charming 2 room guest house, access to Pool, A\/C, & WiFi, Key West, near Duval$
From $1179 per night (USD)
VRBO
Charming 2 room guest house, access to Pool, A\/C, & WiFi, Key West, near Duval
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Key West is waiting for you at this clean & spacious 2-bedroom guest house. Good for up to 6 people. This cozy retreat o ...
From $1179 per night (USD)
VRBO
From $2443 per night (USD)
VRBO
Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Explore the city the ...
From $2443 per night (USD)
VRBO
$Outstanding Room w\/ King Bed & Patio just steps from Duval St - Key West Bliss$
From $806 per night (USD)
VRBO
Outstanding Room w\/ King Bed & Patio just steps from Duval St - Key West Bliss
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $806 per night (USD)
VRBO
$1BR Suite w\/ Spacious Living Area and Access to Heated Pool, Near Duval St$
From $973 per night (USD)
VRBO
1BR Suite w\/ Spacious Living Area and Access to Heated Pool, Near Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $973 per night (USD)
VRBO
$Welcoming 2 Queen Room w\/ Patio- Heart of Key West$
From $875 per night (USD)
VRBO
Welcoming 2 Queen Room w\/ Patio- Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $875 per night (USD)
VRBO
$Room w\/ Queen Bed w\/ Patio in the Heart of Key West - Duval St steps away$
From $816 per night (USD)
VRBO
Room w\/ Queen Bed w\/ Patio in the Heart of Key West - Duval St steps away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $816 per night (USD)
VRBO
From $1870 per night (USD)
VRBO
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1870 per night (USD)
VRBO
From $723 per night (USD)
VRBO
Vibrant 2 Floor Loft Ideal for Relaxing Escape in Key West - Near Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $723 per night (USD)
VRBO
$Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away$
From $422 per night (USD)
VRBO
Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $422 per night (USD)
VRBO
From $1127 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $1127 per night (USD)
VRBO
From $933 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $933 per night (USD)
VRBO
From $153 per night (USD)
VRBO
Contemporary Hideaway in the Heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. E ...
From $153 per night (USD)
VRBO
From $2236 per night (USD)
VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)
VRBO
From $1759 per night (USD)
VRBO
Parrot Key | Beachfront | Kitchen | Hot Tub | Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step into a paradise of white sands and glimmering pools, where boat drinks and watersports are just steps away at Parro ...
From $1759 per night (USD)
VRBO
From $1941 per night (USD)
VRBO
The Banyan | Concierge | Beach Access | Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1941 per night (USD)
VRBO
From $1759 per night (USD)
VRBO
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1759 per night (USD)
VRBO
From $11524 per night (USD)
VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $11524 per night (USD)
VRBO
From $2236 per night (USD)
VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)
VRBO
From $1759 per night (USD)
VRBO
Coconut Beach | Beach | Concierge | Pool | Gym
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1759 per night (USD)
VRBO
From $2148 per night (USD)
VRBO
Hyatt Beach | Concierge | Spa | Pool | Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $2148 per night (USD)
VRBO
From $1839 per night (USD)
VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $1839 per night (USD)
VRBO
From $1733 per night (USD)
VRBO
Sleeps 6 | Hyatt | Lux Resort | Concierge | Pool | Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set along the stunning Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly blends Key West’s laid-back vibe with mod ...
From $1733 per night (USD)
VRBO
From $1771 per night (USD)
VRBO
Sleeps 6 | Lux Resort | Hot Tub | Pool | Concierge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $1771 per night (USD)
VRBO
From $494 per night (USD)
VRBO
Stunning 2BD Oceanfront Escape, Breathtaking Views - pool, hot tub and more
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Côte du Bonheur, your oceanfront retreat located in Key West. This 3rd Floor-level unit in the prestigious 18 ...
From $494 per night (USD)
VRBO
From $701 per night (USD)
Expedia
Atlantis House- beautiful residence close to beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to the Atlantis House, a beautiful vacation rental located in the heart of the charming island town of Key West. ...
From $701 per night (USD)
Expedia
From $1145 per night (USD)
VRBO
Charming Bungalow Perfect for Families and Couples': Escape in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $1145 per night (USD)
VRBO
From $1779 per night (USD)
VRBO
2 Family-friendly Units, Complimentary Breakfast, Outdoor Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1779 per night (USD)
VRBO
From $1035 per night (USD)
VRBO
Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1035 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This 3-bedroom house is perfect for your escape to Key West. This cozy retreat offers prime location near all the action ...
From $407 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Charming 1-bedroom apartment with WiFi, AC in delightful Key West Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Key West adventure begins at this fabulous 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for ...
From $203 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Step into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the cov ...
From $238 per night (USD)
VRBO
From $253 per night (USD)
VRBO
2 Bedroom Townhome in the Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
**Beautiful 2-Bedroom Townhome in Key West Golf Club** Welcome to this charming 2-bedroom, 2.5-bathroom townhome locate ...
From $253 per night (USD)
VRBO
From $527 per night (USD)
Expedia
**A BEACHY VIEW @ THE TRUMAN ANNEX IN KEY WEST**
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $527 per night (USD)
Expedia
From $462 per night (USD)
VRBO
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $462 per night (USD)
VRBO
From $125 per night (USD)
Expedia
Serene Key West Studio with Poolside Peace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio Apartment for Rent in Key West This cozy studio apartment is located in a quiet, gated community on Grinnell Str ...
From $125 per night (USD)
Expedia
From $1824 per night (USD)
VRBO
3| Galleon | Marina | Spa | Hot Tub | Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1824 per night (USD)
VRBO
From $660 per night (USD)
Expedia
3-bedroom townhome in Key West with fitness room, WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Key West at this lovely townhome. With 3 bedrooms including 2 king beds and 2 queen beds, th ...
From $660 per night (USD)
Expedia
From $1031 per night (USD)
VRBO
Atlantis House Suites
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled within the serene enclave of the Atlantis House Compound, the Palm and Banyan Suites offer a tropical oasis for ...
From $1031 per night (USD)
VRBO
From $728 per night (USD)
Expedia
Coco's Poolside Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Coco's Poolside Retreat is a 3-story Key West vacation rental townhouse situated in a one-of-a-kind private tropical poo ...
From $728 per night (USD)
Expedia
From $1558 per night (USD)
VRBO
The Flower Power House - Boho Beautiful
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
Boho beautiful, the free-spirited presence of the Key West Flower Power House vacation rental, has much more in common w ...
From $1558 per night (USD)
VRBO
$VIRGINIA VISTA - Steps from Duval, 2B\/R, 2 Bath Retreat with Pool & Large Porch$
From $295 per night (USD)
VRBO
VIRGINIA VISTA - Steps from Duval, 2B\/R, 2 Bath Retreat with Pool & Large Porch
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a few houses off Duval on Virginia Street, VIRGINIA VISTA occupies the upper level of an almost 100-year-old home i ...
From $295 per night (USD)
VRBO
$VIRGINIA VERANDA, Stylish Old Town 2 B\/R, 2Bath, with Pool, Steps from Duval$
From $293 per night (USD)
VRBO
VIRGINIA VERANDA, Stylish Old Town 2 B\/R, 2Bath, with Pool, Steps from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just a few houses off Duval, this wonderful 2 Bedroom, 2 Bath retreat occupies the ground level of an almost 100-year-ol ...
From $293 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Palm Isle! A tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front ...
From $363 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Garden of Roses | Private Hot Tub, Prime Key West Location! - Monthly Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Garden of Roses | Private Hot Tub, Prime Key West Location! Experience the essence of Key West living at Garden of Rose ...
From $293 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Charming 2-Bedroom Retreat with Golf Course Views | Key West Golf Club Community Nestled in the picturesque Key West Go ...
From $220 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Key West vibes, 2-bedroom townhome with AC, WiFi in marvelous Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Key West, this delightful townhome boasts 2 bedrooms with a king bed and a full bed, perfect for a small grou ...
From $263 per night (USD)
VRBO
From $195 per night (USD)
Expedia
Gypsyginny's Hideaway in downtown Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Set in the heart of Key West's vibrant Meadows district, this delightful 3-bedroom vacation rental on iconic White Stree ...
From $195 per night (USD)
Expedia
$Duval Hideaway | Dog-Friendly Home w\/ Shared Hot Tub, Patio & Prime Location$
From $605 per night (USD)
VRBO
Duval Hideaway | Dog-Friendly Home w\/ Shared Hot Tub, Patio & Prime Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Duval Hideaway | Dog-Friendly Home with Shared Hot Tub, Patio & Prime Location Duval Hideaway is the perfect home base ...
From $605 per night (USD)
VRBO
$Duval Street Retreat | Dog-Friendly Home w\/ Hot Tub, Patio, & Parking$
From $605 per night (USD)
Expedia
Duval Street Retreat | Dog-Friendly Home w\/ Hot Tub, Patio, & Parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Duval Street Retreat | Dog-Friendly Home with Hot Tub, WiFi, & Private Parking Duval Street Retreat is your ideal Key W ...
From $605 per night (USD)
Expedia
From $2319 per night (USD)
VRBO
Meadows Manor | Elegant Oasis with Private Pool & Parking! Weekly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Meadows Manor | Elegant Oasis with Private Pool & Parking Discover the perfect blend of luxury and tranquility at the M ...
From $2319 per night (USD)
VRBO
From $185 per night (USD)
Expedia
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, Close to Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, and Close to Beach! Salt Pond Hideaway is your ideal retreat ...
From $185 per night (USD)
Expedia
From $1198 per night (USD)
VRBO
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Southernmost Retreat | Two Dog-Friendly Homes with Hot Tubs, WiFi, & Private Parking Southernmost Retreat is the perfec ...
From $1198 per night (USD)
VRBO
From $1826 per night (USD)
VRBO
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1826 per night (USD)
VRBO
From $360 per night (USD)
VRBO
Kingfish Keep | Lively Escape on Duval! Balcony!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Kingfish Keep | Lively Escape on Duval! Balcony! Kingfish Keep is the perfect escape in the heart of the historic distr ...
From $360 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Yellowfin Ledge | Inviting Getaway On Duval! Balcony! Yellowfin Ledge is the ideal choice for your Key West adventure! ...
From $360 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Wahoo Way | Charming Hideaway On Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wahoo Way | Charming Hideaway On Duval Street! Escape to Wahoo Way for an unforgettable couple’s retreat in Key West! T ...
From $352 per night (USD)
VRBO
From $1075 per night (USD)
Expedia
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street! Pescado Penthouse is the ultimate getaway for families or ...
From $1075 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Key West Retreat! 3-bedroom house in fabulous Key West with AC, WiFi.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Located in Key West, this gorgeous house boasts 3 bedrooms - one with a king bed, one with a queen bed, and one with a t ...
From $250 per night (USD)
VRBO
From $155 per night (USD)
VRBO
Charming 1-bedroom apartment in Key West with AC, WiFi. Enjoy
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this brilliant apartment. This marvelous space features 1 bedroom with a queen b ...
From $155 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Poolside Hide-Away is a first floor one bedroom, one bath historic condo, that can accommodate up to 4 people, with wrap ...
From $425 per night (USD)
VRBO
From $685 per night (USD)
Expedia
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quai ...
From $685 per night (USD)
Expedia
$WASTIN' A WAYLAND ~ Renovated 2 BR\/2 Ba Home in Old Town!$
From $242 per night (USD)
VRBO
WASTIN' A WAYLAND ~ Renovated 2 BR\/2 Ba Home in Old Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
OLD TOWN GEM... This 2 bedroom, 2 bathroom cutie resides down a charming lane surrounded by historic residences and is a ...
From $242 per night (USD)
VRBO
From $1683 per night (USD)
Expedia
**HOUSE OF THE ROYAL PALMS @ OLD TOWN** Estate & Pool Near Duval + LAST KEY SERV
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $1683 per night (USD)
Expedia
From $1389 per night (USD)
VRBO
**The Three Mermaids @ Solaris Hill** New Construction Compound + Last Key Servi
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finding a com ...
From $1389 per night (USD)
VRBO
$INTO THE BLUE ~ Pristine 4 BR\/3.5 Bath Home w\/ Private Pool!$
From $440 per night (USD)
Expedia
INTO THE BLUE ~ Pristine 4 BR\/3.5 Bath Home w\/ Private Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
TOP NOTCH LIVING… Nestled in the exclusive Casa Marina district, this newly constructed sanctuary sits only a few blocks ...
From $440 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Cozy on Caroline - Key West Seaport
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Experience the quintessential Key West lifestyle in this charming one-bedroom, two-bathroom apartment that perfectly bal ...
From $265 per night (USD)
VRBO
From $353 per night (USD)
Expedia
On the Bright Side of the Key West Golf Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to your serene retreat at The Key West Golf Club! This meticulously cared-for 3-bedroom, 3-bathroom townhome rad ...
From $353 per night (USD)
Expedia
From $541 per night (USD)
VRBO
Royal Palm of Casa Marina
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
EXQUISIT NEW CONSTRUCTION HOME!!!! Discover the epitome of modern luxury and comfort at this brand-new exquisite 4-bedr ...
From $541 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Southern Skies, Stylish Home in Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart of Key West's His ...
From $416 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Seaport Serenity Cottage - Quiet and Quaint
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2BR/2BA rental is located in the Historic Seaport District offering off-street parking and a prime locatio ...
From $287 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Rooster Doodle Do - Midtown Family Retreat
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Your perfect tropical getaway! This stunning 3-bedroom, 3-bathroom home with an additional guest cottage is designed for ...
From $402 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Charming 1923 2 Bedroom, 1 Bath home with bonus loft.
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to The Emma House! A delightful 1923 Key West retreat located in the heart of historic and vibrant Bahama Villa ...
From $261 per night (USD)
VRBO
From $182 per night (USD)
VRBO
Charming Cottage in Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your Key West adventure begins at this charming 1-bedroom cottage. The lovely bedroom features a comfortable queen bed, ...
From $182 per night (USD)
VRBO
From $646 per night (USD)
VRBO
Amazing Key West location 3 bed 3 bath home, with HEATED PRIVATE POOL, WIFI
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $646 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Quaint 2-bedroom + Loft house in old town Key West. Blocks to beach & Duval St.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Nestled in the heart of old town Key West, this delightful unit boasts 2 cozy bedrooms with queen beds and a spacious lo ...
From $310 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Beachfront Condo in heart of Key West, minutes to downtown 1BR-1BA 2 lg pools 🚲
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Key West-Resort style living! Spacious 1 bed/ 1 bath, large living space full-kitchen condo in gated community. Beachf ...
From $193 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Zen Villa - A Luxe Retreat in the Heart of Old Key West! Tucked away on a quiet lane just steps from the vibrant heartbe ...
From $504 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Jerry's Escape - Truman @ Duval | Cozy Studio Perfect for Couples
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Truman @ Duval - Unit C | Cozy Studio Perfect for Couples Experience your perfect romantic retreat, offering a charming ...
From $375 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Truman @ Duval - Unit D | Two-Bedroom with Full Kitchen & Prime Location Welcome to your perfect family getaway in the ...
From $581 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Ricky's Retreat - Truman @ Duval | Perfect for a Getaway in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval Unit A | Perfect for a Getaway in Key West Escape to this cozy, vibrant cottage in the heart of downtown ...
From $368 per night (USD)
VRBO
From $375 per night (USD)
Expedia
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Scott's Cottage - Truman @ Duval F | Perfect Location! Ideal for Solos & Couples Looking for a relaxing retreat in the ...
From $375 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval - Unit E | Cozy Getaway in the Heart of Key West Duval Studio is your perfect launchpad for an unforgett ...
From $366 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Slice of Paradise | 3 bedroom, 2 bathroom pool home in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover your island oasis in this beautifully updated one-story home, where tropical breezes meet modern comfort. Nestl ...
From $276 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Key West 2 BR Villa with full kitchen, ocean view with Infinity pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in Key West just minutes from beautiful sunsets at Mallory Square or renowned dining and nightlife of Duval Stre ...
From $450 per night (USD)
VRBO
From $495 per night (USD)
VRBO
Tropical Island Retreat Near Florida Beaches with Pool & Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stylish, pet-friendly, and amazing decor is what awaits you. This boutique hotel offers you a great stay in the heart of ...
From $495 per night (USD)
VRBO
From $512 per night (USD)
VRBO
Tropical Island Retreat Near Florida Beaches with Pool & Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $512 per night (USD)
VRBO
From $604 per night (USD)
VRBO
Charming Hideaway with Pool – Walk to Duval St & Local Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $604 per night (USD)
VRBO
From $612 per night (USD)
VRBO
Sunny Florida Escape with Pool, Beach Access & Stunning Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $612 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Cozy Key West Escape – Near Shops, Bars & Famous Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $535 per night (USD)
VRBO
$CASA DEL SUR ~ Renovated 2 BR\/2Ba Home with Dip Pool & Outdoor Spa!$
From $608 per night (USD)
VRBO
CASA DEL SUR ~ Renovated 2 BR\/2Ba Home with Dip Pool & Outdoor Spa!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
QUAINT AND PRIVATE HIDEAWAY... This Key West classic checks all the boxes for your blissful getaway to our tiny island p ...
From $608 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Cozy & modern guest house in Key West with AC, WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Your cozy getaway awaits in Key West at this marvelous apartment. With a bedroom, washing & drying machine, AC, and WiFi ...
From $193 per night (USD)
Expedia
From $935 per night (USD)
VRBO
Ocean Front Balcony King at Southernmost Beach Resort!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the best of Key West, where modern design meets a romantic, tropical setting. Nestled just steps away from le ...
From $935 per night (USD)
VRBO
From $488 per night (USD)
VRBO
Key West Comfort | Bungalow with Patio, 3 Pools & Steps to Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $488 per night (USD)
VRBO
From $735 per night (USD)
VRBO
Central Key West Stay | 3 Pools, Free Daily Breakfast, Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $735 per night (USD)
VRBO
From $573 per night (USD)
VRBO
Tropical Bungalow, 3 Pools, Breakfast Included, Pets Allowed, Near Shops & Bars
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $573 per night (USD)
VRBO
From $478 per night (USD)
VRBO
Pet-Friendly & Cozy Bungalow, Daily Breakfast & Poolside Lounging!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $478 per night (USD)
VRBO
From $541 per night (USD)
VRBO
Bungalow in Heart of Key West | 3 Pool, Free Breakfast, Shops & Bars Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $541 per night (USD)
VRBO
From $482 per night (USD)
VRBO
Key West Charm | 3 Pools, Complimentary Breakfast, Near Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $482 per night (USD)
VRBO
From $616 per night (USD)
VRBO
Key West Getaway | Romantic Bungalow, Pools, Breakfast & Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $616 per night (USD)
VRBO

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